PT1278757E - Preparation of secondary aminoisobutylalkoxysilanes - Google Patents

Abstract

A highly efficient method is provided for preparing secondary aminoisobutylalkoxysilanes by reacting hydridoalkoxysilanes with secondary methallylamines in the presence of a hydrosilation catalyst.

Description

DESCRIPTION OF THE PREPARATION OF AMINOISOBUTILALCOXYSILANES SECONDARY "

Field of the Invention The present invention relates to a highly efficient method of preparing secondary aminoisobutylalkoxysilanes by noble metal catalysed hydrosilation reactions between secondary metalylamines and hydridoalkoxysilanes.

Background of the Invention

Secondary aminoisobutylalkoxysilanes have long been accessible by various chemical approaches, and have recently demonstrated commercially useful performance in polyurethane seals providing sites for crosslinking functional alkoxysilane polyurethanes (see EP 676403). However, the preparation of these silanes has been done with some degree of complexity. The preparation of Me (MeO) 2SiCH2CHMeCH2NHMe is described (Journal of Organic Chemistry, vol.33, 3120 (1971)) through a series of reactions including hydrosilation of methallyl chloride with MeSiHCl2, reaction of that product with a large excess of MeNH2 and reaction of the cyclic silazane, thus formed with MeOH. A similar version of trialkoxysilane was prepared by a slightly different reaction sequence as described in Brit. 994044 wherein methallyl chloride is hydrosilated with trichlorosilane followed by reaction of said product with ethanol to form (EtO) 3SiCH 2 CHMeCH 2 Cl and reaction of that product with excess MeNH 2 to form (EtO) 3 Si CH 2 CHMeCH 2 NHHMe 3. These two processes involve both three steps, namely hydrosilation, esterification and amination, plus a final purification, such as by distillation, such that these processes are not commercially or economically attractive. While bis (alkoxysilyl isobutyl) amines, the putative hydrosilylations of dimethallylamine with hydridoalkoxysilanes or hydridoalkylalkoxysilanes, would be very difficult to prepare by the above procedure involving cyclic silazane intermediates, are described as low yielding by-products of the latter process involving reactions of chloroisobutylalkoxysilanes with ammonia. Also described is a similar molecule as a byproduct of the reduction of 2-cyanopropylethoxysilane (U.S. 2930809) and as a crosslinked aminosiloxane resin stock prepared by reaction of chloroisobutyltriethoxysilane with ammonia (U.S. 4,410,669 and 4, 44554). The product of EP 676403, namely Me (MeO) 2SiCH 2 CHMeCH 2 NHC 6 H 5, was prepared by reacting excess aniline with Me (MeO) 2 Si CH 2 CHMeCH 2 Cl, and involves the above three further distillation steps.

There is thus a continuing need in the art for secondary aminoisobutylalkoxysilane adhesives and sealants, including secondary bis (alkoxysilylisobutyl) amines, which can be prepared in high yields and at high purities by processes which are efficient both in terms of reaction time and production per unit volume of equipment used, producing minimum quantities of waste and by-products and which are simple in terms of the number of steps in the process and the number of raw materials, additives or promoters to be loaded on the equipment. Methallylamine is described and / or claimed in several patents involving the hydrolysis of allyl amines using hydroxysiloxanes, but there is no example of application of such a reaction, and hydrolysylation of metalamine using a hydroxysilane has not been suggested. In particular, there is a description of the hydrosilation of a secondary methallylamine with a hydroxysiloxane (U.S. 5,448,634) and a limited technique on tertiary metalloamine hydrosilations, which would yield products of no utility in the protection of polyurethanes. There is also no example of the application of dimethallylamine hydrosilation, although such an amine is described in at least one hydrosilation patent also involving hydroxysiloxanes (U.S. 5,840,951).

Historically, the hydrosilations of allylic amines have been known to be unsuccessful. Allylamine is specifically excluded from an initial general patent on hydrosilation (US 2970150), the hydrosilation products being prepared by protection of allylamine with trimethylsilyl groups, hydrolysis of the allyl group and removal of the trimethylsilyl groups (see Journal of Organic Chemistry, Vol. 24,119 (1959)).

Alternatively, aminopropylalkoxysilanes were prepared by reactions of chloropropylalkoxysilanes with large excesses of ammonia or primary amines, giving the respective primary or secondary aminopropylalkoxysilanes. These routes suffer from low yields per unit volume of equipment used, high levels of residues or excess of raw materials and the formation of large amounts of hydrochloride salts, solids difficult to handle. The aminopropylalkoxysilanes were also prepared by reduction of cyanoethylalkoxysilanes, which are prepared by hydrolysis of 3-acrylonitrile with chlorosilanes, followed by esterification with the appropriate alcohol. These are multi-step processes, followed by purification, as by distillation. Various further developments have allowed noble metal catalysed hydrosilations of allylamine with various SiH-containing reagents, although the reactions have been impractical because they are slow and / or incomplete, unless performed at the higher temperature, usually under pressure, in the presence of a hydrosilation promoter (US 4481364). Further improvements in yields were obtained with rhodium catalysts instead of platinum catalysts, with additives or promoters being required for both said improved yields and to provide products with decreased levels of unwanted internal isomeric adducts (US Pat. Nos. 4,55,622; US 4,888,436; US 4,897,501 US 4921988, US 4927953). The diallylamine-related situation is further complicated by the formation of disproportionation side products, which do not occur with the allylamine itself (Zhur Obshch, Khim.r Vol. 44, 1484 (1974), in English as Journal of General Chemistry, USSR , Vol. 44, 1456 (1974)).

Against this background there was previously no reason to predict that the secondary aminoisobutylalkoxysilanes could be prepared in high yield by a direct hydrosilylation reaction of an alkoxyhydrosilane and a metalylamine compound. EP-A-0135813 describes a palladium-catalyzed addition of alkylamine and trialkoxysilones under pressure at 110-120 ° C.

Summary of the Invention The present invention provides a simple and highly effective method for the preparation of secondary aminoisobutylalkoxysilanes by the noble metal catalysed hydrosilation of secondary metalylamines with hydridoalkoxysilanes or hydridoalkylalkoxysilanes. The reactions proceed in high yields and conversions to yield isomerically pure products in the absence of additives or promoters normally required for hydrolysates of allyl amines. The process involves neither the modification of the secondary metalylamines nor the use of the addition of hydrosilation promoters or solvents. Standard noble metal catalysts can be used. The invention as claimed is set forth in more detail in the appended claims.

Detailed Description of the Invention 5 aryloxy, alkaryloxy or aralkyloxy having 6 to 10 carbon atoms, R 3 represents an alkyl group having 1 to 6 carbon atoms or an aryl, alkaryl or aralkyl group having 6 to 10 carbon atoms; a is 0, 1 or 2; U represents a linear, cyclic or branched divalent hydrocarbon group having 1 to 6 carbon atoms which may optionally be interrupted by one or more ether oxygen atoms and / or substituted with a carbonyl oxygen atom; m is 0 or 1 or u is 0 or 1 / T is - (U-Om) u-CH 2 -CH (CH 3) -CH 2 -; X is an alkylene group having 3 to 11 carbon atoms or T; and Cat represents an effective amount of a noble metal-containing hydrosilation catalyst.

Examples of compounds of formula I include (MeO) 3SHH, Me (MeO) 2SiH, Me 2 (MeO) SiH, (EtO) 3SH, Me (EtO) 2SiH, Me 2 (EtO) SiH, or (PrO) 3SiH, Me ) 2 SiH and Me 2 (PrO) SiH wherein Me is methyl, Et is ethyl and Pr is n-propyl or i-propyl; the corresponding butoxy, pentoxy or hexoxy silanes; phenoxysilanes such as Me (C 6 H 5 O) 2 SiH, C 6 H 5 (MeO) 2 SiH; and the like. Preferred are methoxy and ethoxysilanes, particularly trialkoxysilanes prepared by the direct reactions of silicon metal with the corresponding alcohol. Also preferred are the methyldialkoxysilanes, normally prepared by esterification of the respective hydridodichlorosilane with the corresponding alcohol.

In general, the compounds of Formula II will comprise at least one methallyl group and a secondary amine group, and may contain other hydrocarbon and oxygen functionalities, with the proviso that said functionalities do not interfere with the hydrolysylation reactions. Examples of compounds of Formula II include CH2 = CMeCH2NHMe, CH2 = CMeCH2NHEt, CH2 = CMeCH2NHPr, 6 CH2 = CMeCH2NHBu wherein Et is ethyl and Pr and Bu are linear or branched propyl and butyl, CH2 = CMe CH2 NHC6H5, CH2 = CMe CH2 NHCH2 C6 H5, CH2 = Wherein R 3 is as defined above and ebec are integers from 0 to 10, and b + c are at least 2, CH 2 = CMeCH 2 NHCH 2 CH 3 (CH 2 CO 2 R 3), CH 2 CH 2 CH 2 CH 2 CH 2 CH 2 CH 3, wherein R 3 is as defined above, (CH 2 = CM e CH 2) 2 NH, (CH 2 = CM e CH 2 CH 2 CH 2) 2 NH, and the like. Preferred is CH2 = CMeCH2NHC6H5, CH2 = CMeCH2NHCH2C6H5, CH2 = CMeCH2NHCH2CH20R3, CH2 = CMeCH2NHCH2CHMeOR3, CH2 = CMeCH2 NH (CH2 CH2) b (CH2 CH2 O) CR3, wherein R3 is as defined above and ebec are integers from 0 to 10, and b + c are at least 2, CH2 = CMeCH2NHCHC02R3 (CH2CO2R3) wherein R3 is as defined above, (CH2) m CH2 CH2 2NH, (CH2 = CMeCH20CH2CH2) 2NH, and the like. A preferred compound of Formula 11 is N-ethylmethallylamine; another is N-phenylmethallylamine and a third is dimethallylamine. The hydrosilation catalyst is a platinum containing hydrosilation catalyst. The platinum-containing hydrosilation catalyst of the present invention may be used in any catalytically effective form, including in its compounds or solutions and as deposits in various organic or inorganic supports. Preferred catalysts are chloroplatinic acid and its solutions and the platinum and divinyltetramethyl disiloxane complex and their solutions. The level of catalyst is an effective amount to catalyze the reaction and will typically be in the range of from about 5 to about 500 parts per million of noble metal over the combined weights of the reactants of Formulas I and II, with 10 to 100 parts per million.

The reaction conditions are not critically so defined with respect to temperature, pressure, proportions of reagents 7 or order of combination of the reactants. The reaction temperature is raised, in the range of 50 to 150 ° C, with 60 to 120 ° C being preferred. The reactions will be carried out at atmospheric pressure. The ratio of the reactants, i. the molar ratio of the reagent of Formula I to that of Formula II ranges from 0.2: 1 to 5: 1, but is generally close to 1: 1 for secondary metallylamines with a methallyl group, and about 2: 1 for dimethallylamines. For economic reasons a slight excess of the reagent of Formula I, for example a ratio of 1.2: 1 to monometalylamines or 2.4: 1 to dimethallylamines, is preferred.

These hydrosilation reactions can also be carried out continuously in equipment designed for this purpose (see, for example, U.S. 6,015,920). The reaction times are relatively short for these reactions, which are exothermic. This last point implies that the catalysis of the total mixture of compounds of Formulas I and II is less desirable from a safety point of view.

An unexpected feature of the present invention is that there is no need for additives or promoters other than the hydrolysylation catalyst. There is no problem of the formation of internal adduct isomers, and there is no problem of dehydrocondensation reactions between hydroxysilyl groups and secondary amine groups leading to Si-N bond formation and hydrogen production. This is particularly surprising in view of the poor reactivity of the primary metalylamine, CH 2 = CH 2 CH 2 NH 2, under the same reaction conditions. The efficient reactivity of secondary metalylamines extends to dimethallylamine, which does not present any of the serious problems of formation of by-products, namely formation of internal adducts and disproportionation products, attributed to diallylamine. Thus, while the various additives and promoters and the high reaction and pressure temperatures which have been used for the allylamine can be used with secondary metallamines, it is neither necessary nor necessary to modify the secondary methallylamines with trilmethylsilyl groups to allow the hydrosilation. Thus, while many process patents dealing with allylamine hydrosilation require the use of additives, promoters, high temperatures or high pressures, and have claims including metalylamines, it has surprisingly been found that the secondary metalylamines are hydrosilyated with hydridoalkoxysilanes or hydridoalkylalkoxysilanes, without using any of said processes. There is a secondary reaction which is perhaps more prevalent in the preparation of secondary aminoisobutylalkoxysilanes than in the preparation of primary or secondary aminopropylalkoxysilanes. This secondary reaction, which ultimately leads to the same desired product as the hydrosilation reaction, is the formation of cyclic silazanes by reaction of the secondary amine group with the alkoxysilane group. Generally speaking, the product of Formula III cyclizes to a cyclic silane of Formula IV with the production of one molar equivalent of alcohol, R 3 H, wherein is as defined above. This reaction is illustrated below: R1NH-T-SiR3a (R2) 3-a R1N-SiR3a (R2) 2-a + r2r /

T

III Formation of cyclic silazane is an equilibrium reaction, displaced to the right by the removal of alcohol, R 3 H. The simple addition of the appropriate alcohol equivalent, R 3 H, to the cyclic silane-containing product IV will regenerate the desired product. Removal of the cyclic silazane impurities is a necessary part to ensure purity of the product for stoichiometric calculations used in the preparation of silylated polyurethanes.

It should also be noted that the products of the present invention, after distillation to remove excess reactants and excess alcohol, if used to remove impurities from cyclic silazanes, are of sufficient purity to be used without further purification (eg by distillation) in many applications. This stems from the fact that there is no mechanism for producing high boiling bis-silyl side products in both the chloroisobutylalkoxysilane and ammonia reactions and reduction of 2-cyanopropylalkoxysilanes with hydrogen. Distillation may be desirable in some cases, however, to provide an incremental increase in purity and / or to remove color and catalyst residues.

The methyl / alkoxy group exchange reaction, recently observed in other hydrolysates of methyldialkoxysilanes (see copending application Serial No. 09 / 481,444, Filipkowski et al., Incorporated herein by reference), does not occur to a significant extent during hydrosilylation of secondary metalylamines.

The following specific examples illustrate certain aspects of the present invention and, more particularly, point out various aspects of the method for its evaluation. However, the examples are presented for illustrative purposes only and are not to be construed as limitations of the present invention.

EXAMPLES 10

The abbreviations g, mL, L, mm, mol, mmol, ppm, yL, h, kg, kmol, GC and MS respectively represent gram, milliliter, liter, millimeter, molar equivalent, millimolar equivalent, parts per million, microliter, hour , kilogram, chilomolar equivalent, gas chromatography and mass spectrometry. All temperatures are expressed in degrees Celsius and all reactions are carried out on standard laboratory or pilot scale glassware or production units at atmospheric pressure under an inert atmosphere of nitrogen and all parts and percentages are by weight.

Example 1 outside the scope of claims Hydrosilation of N-Ethylmetallylamine with Trimethoxysilane

A one-neck, three-necked round bottom flask was equipped with a magnetic stir bar, running heating mantle, thermocouple, addition funnel, condenser and N2 inlet / bubbler. The flask was charged with 220 g (1.80 mol) of trimethoxysilane and heated to 60 ° C at which temperature was added 0.25 ml of platinum tris (divinyltetramethyl disiloxane) diplatin (0) (5% Pt content in toluene - referred to as Pt catalyst throughout these examples). The solution was further heated to 68øC and the dropwise addition of 150 g (1.52 moles) of N-ethylmethylallylamine was then carried out over a period of 45 minutes. After the addition, the mixture was heated to 90 ° C and held at this temperature for 1 h. The temperature was then raised to 105 ° C and held for 4.5 h. After completion of the reaction, the mixture was cooled to room temperature and 16 g (0.5 mol) of methanol was added and gently heated before distillation. Final purification by vacuum distillation gave 273 g (1.24 moles) of N-ethyl-3-trimethoxysilyl-2-methylpropanamine. The product (bp 98-100 ° C at 12 mm Hg) was characterized by GC / MS. The yield of isolated product was 82%. The structure of the product was confirmed by GC / MS analysis.

Example 2 - Hydrosilation of N-Ethylmetallylamine with Methyldiethoxysilane

Except for a distillation head replacing the condenser, the apparatus was similar to that of Example 1. The flask was charged with 381 g (2.84 moles) of methyldiethoxysilane and 0.65 ml of platinum catalyst. The contents were heated to 90 ° C and 260 g (2.63 moles) of N-ethylmethallylamine was added over 30 minutes through an addition funnel. Immediately after the addition was complete, the mixture was heated to 110øC and held for one hour. The product was isolated by vacuum distillation to give 485 g (2.08 mol) of N-ethyl (3-diethoxymethylsilyl) -2-methylpropanamine. The product (bp 88-90øC at 27 mm Hg) was characterized by GC / MS. The yield of isolated product was 79%. 12

Example 3 outside the scope of the claims - Hydrosilation of N-Ethylmetallylamine with Trimethoxysilane To a jacketed 50 L glass reactor equipped with a refluxing column was added 16.8 kg (167 moles) of N-ethylmethallylamine and 42 ml of platinum catalyst. The mixture was then heated to 93øC and 24.9 kg (204 moles) of trimethoxysilane was added slowly over 4 h. After the addition was complete, the reaction mixture was heated to 105 ° C and held for 2 h. After the warm-up period, the mixture was cooled to below 50 ° C and 1.5 L of methanol was added. The crude material was distilled to give 28.9 kg (131 moles) of material with a purity of 99%. The isolated yield of N-ethyl-3-trimethoxysilyl-2-methylpropanamine was 78% based on N-ethylmetallylamine.

Example 4 outside the scope of the claims - Hydrosilation of N-Ethylmetallylamine with Trimethoxysilane To a 500 gallon reactor was added 489 kg (4.94 kmoles) of N-ethylmetallylamine and 1425 g of platinum catalyst. The resulting solution was heated to 88 ° C and trimethoxysilane (725 kg, 5.94 kmoles) was added at such a rate that the temperature remained below 105 ° C. After the addition was complete, the contents were heated at 110 ° C for one hour. The low boiling side products were then removed by distillation. The mixture was then cooled and about 60 L of methanol was added, and the reaction mixture was stirred at 50 ° C for 1 hour before removal of excess methanol by distillation. The resulting crude material (purity > 97%) was then transferred from the reactor. The process was repeated without cleaning the reactor to give a combined total of 1638 kg (7.41 kmol) of N-ethyl-3-trimethoxysilyl-2-methylpropanamine.

Example 5 - Hydrolysis of Dimethallylamine with Trimethoxysilane To a 4-necked flask equipped with reflux condenser, addition funnel, heating mantle, thermocouple and a magnetic stirrer was added 12.0 g (0.10 moles) of trimethoxysilane and 17 and platinum catalyst. This mixture was heated to 85 ° C and 5.0 g (0.04 mol) of dimethallylamine was added dropwise. After the addition was complete, the reaction mixture was heated at 110 ° C for 3.5 hours. The resulting mixture was analyzed by qasosa chromatography and GC / MS. Gas chromatography showed that the diadduct was formed in 81% yield based on dimethallylamine.

Example 6 - Hydrolysis of Dimethallylamine with Methyldiethoxysilane The reaction was performed in a similar manner to Example 5 except that the flask was charged with 13.5 g (0.10 mol) of methyldiethoxysilane and 18.5 Âμl of platinum catalyst. This solution was heated to 90 ° C and 5.0 g (0.04 mol) of dimethallylamine was added dropwise. After the addition was complete, the reaction was heated to 105 ° C and held for 6 h. The resulting mixture was analyzed by gas chromatography and GC / MS. Gas chromatography indicated that the diadduct yield was 97% based on dimethallylamine. 14

Example 7 - N-Ethylmethallylamine hydrosilation with

Trimethoxysilane The reaction was performed in a similar manner to Example 5 except that the flask was charged with 5.0 g (0.03 mol) of triethoxysilane and 5æl of platinum catalyst. This solution was heated to 100 ° C and 3.0 g (0.03 mol) of N-ethylmethallylamine was added dropwise. After the addition was complete, the reaction was heated at 130 ° C for 3 h. The resulting mixture was analyzed by gas chromatography and GC / MS. Gas chromatography indicated that the yield of N-ethyl-3-triethoxysilyl-2-methylpropanamine was 85% based on triethoxysilane.

Example 8 - Dimethalylamine hydrosilagen with

Methyldimethoxysilane The reaction was performed in a similar manner to Example 5 except that the flask was charged with 15.0 g (0.12 mol) of dimethallylamine and 44æl of platinum catalyst. This solution was heated to 85 ° C and 28.9 g of methyldimethoxysilane (purity 93.8%, 0.26 moles) was added dropwise. After the addition was complete, the mixture was heated at 122 ° C for two h. The reaction was then cooled and 2 mL of methanol was added. The resulting mixture was analyzed by gas chromatography and GC / MS. Gas chromatography indicated that the yield of the diaduct was 92% based on dimethallylamine. 15

Example 9 - Hydrosilation of N-Ethylmetallylamine with Methyldimethoxysilane The reaction was performed in a similar manner to Example 5 except that the flask was charged with 18 g (0.18 mol) of N-ethylmethallylamine and 40æl of platinum catalyst. This solution was heated to 85 ° C and 22 g of methyldimethoxysilane (purity 95.2%, 0.2 mol) was added dropwise. After the addition was complete, the mixture was heated at 110 ° C for 1.5 h. The resulting mixture was analyzed by gas chromatography and GS / MS. Gas chromatography indicated that the yield of N-ethyl- (3-dimethoxymethylsilyl) -2-methylpropanamine was 95% based on N-ethylmetallylamine.

Comparative Example 1 - Attempted Hydrosilation of Metalylamine with Trimethoxysilane The reaction was performed in a similar manner to Example 5 except that the flask was charged with 10.5 g (0.09 mol) of trimethoxysilane and 16 μl of platinum catalyst. The solution was heated to 85 ° C and 5.0 g (0.07 mol) of methallylamine was added dropwise. The reaction was refluxed for 3.5 hours. Gas chromatography and GC / MS analysis indicated no hydrosilation of the product.

Example 10 - Hydrolysis of N-Phenylmethallylamine with

Trimethoxysilane

To a 100 mL 4 neck round bottom flask equipped with stir bar, thermocouple probe, condenser, addition funnel and nitrogen inlet / outlet was added 12.0 mL 16 (88.3 mmol, 1 , 2 equivalents) of trimethoxysilane (TMS).

A solution of 5% dimethylvinylsiloxane platinum (0) catalyst in toluene (Pt (0) M * M *, 23æl, 20 ppm Pt) was added to the TMS of the reactor. The olefin, N-phenylmethallylamine (67.0 g, 0.52 mol), which had been added to the addition funnel, was then slowly added dropwise to the mixture at ambient temperature. After completion of the addition of the olefin, the slow reaction was slowly heated to a maximum of 80øC over a period of 10+ hours. An additional 30 ppm of Pt (O) catalyst was added over this period to bring the total catalyst charge to 50 ppm platinum. Final GC analysis showed, in addition to unreacted TMS and N-phenylmethallylamine residues, 74.3% of desired product, N-phenyl-3- (trimethoxysilyl) -2-methylpropanamine. The GC / MS data of the above mixture confirms the structure of the product.

The examples and description above are intended to be illustrative and not exhaustive. These examples and description will suggest many variations and alternatives to one of ordinary skill in the art. All such alternatives and variations are intended to be within the scope of the appended claims. Those of ordinary skill in the art will recognize other equivalents of the specific embodiments described herein, which equivalents are also intended to be encompassed by the appended claims. In addition, the specific features described in the dependent claims thereof may be combined in any other way with the features of the independent claims and any of the other dependent claims, and all such combinations are expressly contemplated as being within the scope of the invention.

Throughout the specification and claims the term " comprises " is defined as " includes ", i. and. without limitation of the various defined additional matter to which it may be added, and derivatives of the term (for example " comprising ") are correspondingly.

Lisbon, 2 October 2006 18

Claims (8)

A method for the preparation of a secondary aminoisobutylalkoxysilane comprising the hydrolysis of a secondary methallylamine with a hydridoalkoxysilane in the presence of an effective amount of a platinum-containing hydrosilation catalyst, wherein said effective amount is from 5 to 500 parts per million in weight ratio of noble metal to the combined weight of the hydridoalkoxysilane and the secondary methallylamine, the molar ratio of hydridoalkoxysilane to secondary methallylamine in the range of 0.2 to 5; (B.I) the hydridoalkoxysilane is selected from the group consisting of: triethoxysilane, methyldimethoxysilane, dimethylmethoxysilane, tripropoxysilane, dimethylethoxysilane, methyldipropoxysilane, dimethylpropoxysilane, butoxysilanes, pentoxysilanes, hexoxysilanes and phenoxysilanes; and / or (B.II) the secondary methallylamine is selected from the group consisting of: CH2 = CMeCH2NHMe, CH2 = CMeCH2NHPr, CH2 = CMeCH2NHBu, CH2 = CMeCH2NHC6H5, CH2 = CMeCH2NHCH2C6H5, CH2 = CMeCH2NHCH2CH20R3, CH2 = CMeCH2NHCH2CHMeOR3, CH2 = CMeCH2 NH (CH 2 CH 2 CH 2) 2 NH and (CH 2 = CH 2 CH 2 CH 2 CH 2 CH 2 CH 2) 2 NH, wherein Me is methyl, Pr and Bu 1 are linear or branched propyl and butyl, R 3 represents an alkyl group having 1 to 6 carbon atoms or an aryl, alkaryl or aralkyl group having 6 to 10 carbon atoms, b and c are integers of Oal, and b + c are at least 2; and wherein the hydrosilation step is carried out at an elevated temperature in the range of 50 to 150 ° C and at atmospheric pressure. The method of claim 1 wherein the secondary aminoisobutylalkoxysilane is R1NH-T-SiR3a (R2) 3-a 'the hydridoalkoxysilane is HSiR3a (R2) 3-a' and the secondary metalamine is R1NH- (U-Om) U-CH2C (CH3) = CH2 'wherein R3 represents an alkyl group having 1 to 30 carbon atoms, optionally interrupted with one or more oxygen atoms of ether and / or substituted with a carbonyl oxygen atom, an aryl group, alkaryl or aralkyl of 6 to 10 carbon atoms, or a group of the formula -X-SiR 3a (R 2) 3-a '2 is an alkoxy group having 1 to 6 carbon atoms or an aryloxy, alkaryloxy or aralkyloxy group having 6 to 6 carbon atoms, to 10 carbon atoms, R 3 represents an alkyl group having 1 to 6 carbon atoms or an aryl, alkaryl or aralkyl group having 6 to 10 carbon atoms; a is 0, 1 or 2; U represents a linear, cyclic or branched divalent hydrocarbon group having 1 to 6 carbon atoms and may optionally be interrupted by one or more ether oxygen atoms and / or substituted with a carbonyl oxygen atom; m is 0 or 1; u is 0 or 1; T is - (U-Om) u -CH 2 -CH (CH 3) -CH 2 -, and X is an alkylene group having 3 to 11 carbon atoms or T. The method of claim 2 wherein R 1 represents an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 10 carbon atoms or a group of the formula -X-SiR 3a (R 2) 3-a ' R 3 represents an alkoxy group having 1 to 3 carbon atoms, R 3 represents an alkyl group having 1 to 4 carbon atoms, T represents a branched alkylene radical having 4 to 8 carbon atoms comprising at least one isobutyl group, U represents a terminally unsaturated hydrocarbon having 1 to 4 carbon atoms, X represents an alkylene radical having 3 to 6 carbon atoms or N, 3 The method of claim 1 wherein the hydridoalkoxysilane is selected from the group consisting of triethoxysilane and methyldimethoxysilane; and the secondary metalylamine is selected from the group consisting of N-phenylmetallylamine and dimethallylamine. The method of claim 1 wherein the secondary methallylamine is a compound having a single metallyl or dimethallylamine group, the elevated temperature is in the range of 60 to 120 ° C and the molar ratio of hydridoalkoxysilane to secondary methallylamine is 1 to 1.2 for secondary metallylamines with a metallyl group, and 2 to 2.4 for dimethallylamine. The method of claim 1 wherein the palladium catalyst is selected from the group of homogeneous solutions of chloroplatinic acid and homogenous solutions of platysiloxane vinylsiloxane complexes, and the effective amount represents 10 to 100 parts per million by weight platinum relative to weights of the hydridoalkoxysilane and the secondary methallylamine. The method of claim 1 further comprising adding an alcohol to the reaction product of the hydrosilation step. The method of claim 1 further comprising the subsequent purification of the secondary aminoisobutylalkoxysilane. Lisbon, October 2, 2006 4